cefamandole
Trade name: mandol
Approved
Sep 27, 1978
Cefamandole (also known as cephamandole) is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is an ester form, cefamandole nafate, a prodrug. Cefamandole is no longer available in USA, but it has prescription in UK. Cefamandole under brand name mandol is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms such as: lower respiratory infections, including pneumonia, caused by S. pneumoniae. So as urinary tract infections caused by E. coli, Proteus spp.; peritonitis caused by E. coli and Enterobacter spp. Septicemia caused by E. coli; skin and skin structure infections caused by S. aureus; bone and joint infections caused by S. aureus (penicillinase- and non-penicillinase-producing). Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Bacterial cell wall autolytic enzymes such as autolysins then mediate cell lysis; it is possible that cefamandole interferes with an autolysin inhibitor. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 1 marketing orgs
Timeline
Indications
Mechanism of action
- Bacterial penicillin-binding proteinINHIBITOR
Bacterial penicillin-binding protein inhibitor
Cefamandole is a broad-spectrum cephalosporin antibiotic which belong to a class of beta-lactam antibiotics. ß-lactams disrupt bacterial cell wall biosynthesis by irreversibly inhibiting the D,D-transpeptidases that are responsible for cross-linking the pentapeptide components of polymerized peptidoglycan precursors via specific peptide linkages. This results in the weakening of the bacterial cell wall and causes cell lysis.
- D-alanyl-D-alanine carboxypeptidase DacB (dacB) ↗
- Peptidoglycan D,D-transpeptidase FtsI (ftsI) ↗
- Penicillin-binding protein 1A (mrcA) ↗
- Penicillin-binding protein 1B (mrcB) ↗
- D-alanyl-D-alanine carboxypeptidase DacA (dacA) ↗
- Peptidoglycan D,D-transpeptidase MrdA (mrdA) ↗
- D-alanyl-D-alanine carboxypeptidase DacC (dacC) ↗
Approval history
- approvedPriority reviewSep 27, 1978
Chemistry & pharmacology
SMILES
Cn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](OC=O)c3ccccc3)[C@H]2SC1- Mol. weight
- 490.52 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Discontinued
Oral
No
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1201218 ↗
- WikipediaCefamandole ↗
- NCATS5CKP8C2LLI ↗
- ChEMBLCHEMBL1618 ↗
- ChEMBLCHEMBL1146 ↗
Also known as
- 106223
- (6r,7r)-7-{[(2r)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7r)-7-{[(2r)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7r)-7-(r)-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid
- (6r,7r)-7-(r)-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid
- cefadole
- cefadole
- cefadole
- cefamandol
- cefamandol
- cefamandol
- cefamandole
- cefamandole
- cefamandole
- cefamandole
- cefamandole
- cefamandole
- cefamandole
- cefamandole
- cefamandole
- cefamandole formate sodium
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate
- cefamandole nafate, monosodium salt, 14c-labeled, (6r-(6alpha,7beta,(r*)))-isomer
- cefamandole nafate, monosodium salt, (6r-(6alpha,7beta(r*)))-isomer
- cefamandole nafate sodium
- cefamandole nafate sodium
- cefamandolum
- cefamandolum
- cephadole
- cephadole
- cephadole
- cephamandole
- cephamandole
- cephamandole
- cephamandole
- cephamandole nafate
- cephamandole nafate
- cephamandole nafate
- compound 83405
- compound 83405
- kefadol
- kefandol
- lampomandol
- l-cefamandole
- l-cefamandole
- mandol
- mandol
- mandol
- mandol
- neocefal